Dicyclohexylcarbodiimide → HCID 71243449, 화합물

HRID 1774455노트

반응식

HRID 1774455 반응식
[OH:1][C@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@:3]1([CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1)[C:11]1[CH2:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2.C1CCC(N=C=NC2CCCCC2)CC1.C([NH:63][C@H:64]([C:69](O)=[O:70])[CH2:65][CH:66]([CH3:68])[CH3:67])(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O>CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[NH2:63][C@@H:64]([CH2:65][CH:66]([CH3:68])[CH3:67])[C:69]([O:1][C@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@:3]1([CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1)[C:11]1[CH2:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:70]

참가 물질

6

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 1549133Fmoc-leucineHCID 71243611HCID 71243611, 화합물

생성물 1

HCID 71243449HCID 71243449, 화합물수율 66%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of methyl 4-(((1R,2R)-1-hydroxy-2,3-dihydro-1H,1′H-[2,2′-biinden]-2-yl)methyl)benzoate (10, 180 mg, 0.45 mmol), DCC (112 mg, 0.54 mmol) and DMAP (6 mg, 0.045 mmol) in ethyl acetate (10 mL), was added Fmoc leucine (158 mg, 0.45 mmol) and then stirred at room temperature for 12 h. The solids were filtered, washed with ethyl acetate (25 ml) and the combined filtrate was washed with 1.5 N HCl (25 mL), water (25 mL), brine (10 mL), dried over anhydrous Na2SO4. The organic layer was evaporated under reduced pressure and the residue 1 (250 mg) was dissolved in dry THF (5 mL) and cooled to 0° C. Dimethylamine (5 mL, 20% in THF) was added drop wise and the reaction mixture was slowly allowed to stir at room temperature for 1 h. The reaction mixture was evaporated under reduced pressure and the residue was purified by CombiFlash using 30% ethyl acetate in petroleum ether as an eluent to yield 150 mg (66%) of the title compound as a colorless semi solid.

후처리

  1. filtrationThe solids were filtered
  2. washwashed with ethyl acetate (25 ml)
  3. washthe combined filtrate was washed with 1.5 N HCl (25 mL), water (25 mL), brine (10 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe organic layer was evaporated under reduced pressure
  6. dissolutionthe residue 1 (250 mg) was dissolved in dry THF (5 mL)
  7. temperaturecooled to 0° C
  8. additionDimethylamine (5 mL, 20% in THF) was added drop wise
  9. stirringto stir at room temperature for 1 h
  10. customThe reaction mixture was evaporated under reduced pressure
  11. customthe residue was purified by CombiFlash

출처 및 근거

ORD 기록
ord-efafc5f993fc4b30b0184e15c00459f2
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260376B2

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